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Our top choices for Sheffield hotels

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (46 reviews)
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
The price is Rp3.341.456
Rp3.732.488 total
includes taxes & fees
10 May - 11 May
Wilder House Berkshires

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,005 reviews)
"Great place to stay and close to shops and restaurants will be back!"
United States
Marie-Pascale
The price is Rp1.720.818
Rp1.922.102 total
includes taxes & fees
10 May - 11 May
The Yankee Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (453 reviews)
"Everything was excellent"
United States
Barbara
The price is Rp1.929.402
Rp2.116.554 total
includes taxes & fees
13 May - 14 May
Shaker Mill Inn

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (849 reviews)
"Very clean and cozy in a great location! "
United States
Lidia
The price is Rp1.188.929
Rp1.327.985 total
includes taxes & fees
17 May - 18 May
Monument Mountain Motel

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (932 reviews)
"Great stay!"
United States
Aditya
The price is Rp1.689.530
Rp1.887.204 total
includes taxes & fees
12 May - 13 May
Berkshires Untold

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very good, (1,008 reviews)
"Very friendly staff and conviently located"
United States
Dawn
The price is Rp1.469.648
Rp1.641.597 total
includes taxes & fees
12 May - 13 May
Quality Inn Great Barrington

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (853 reviews)
"Great value"
United States
Ralph
The price is Rp1.369.307
Rp1.529.464 total
includes taxes & fees
18 May - 19 May
Howard Johnson by Wyndham Lenox

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,003 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is Rp1.095.066
Rp1.201.286 total
includes taxes & fees
30 May - 31 May
Pleasant Valley Motel West Stockbridge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (925 reviews)
"Spacious, clean, and the pool was warm and perfect for family swimming "
United States
Danielle
The price is Rp1.520.450
Rp2.085.562 total
includes taxes & fees
26 May - 27 May
Berkshire Mountain Lodge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (25 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is Rp2.894.611
Rp3.233.280 total
includes taxes & fees
20 May - 21 May
Element Lenox Berkshires

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (578 reviews)
"The room was very clean but old and tired. Same with parking area. A decent value when travelling with a pet."
United States
Heather
The price is Rp1.299.975
Rp1.452.159 total
includes taxes & fees
18 May - 19 May
Travelodge by Wyndham Great Barrington Berkshires

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,005 reviews)
"Staff was friendly, room was clean and the beds were comfortable. Dog friendly also. Good breakfast selection. I would stay there again."
United States
Lillian
The price is Rp2.196.216
Rp2.453.122 total
includes taxes & fees
19 May - 20 May
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (417 reviews)
"Clean, good breakfast, friendly staff"
United States
Debra
The price is Rp1.819.965
Rp2.092.960 total
includes taxes & fees
13 May - 14 May
Locust Tree Bed and Breakfast LLC

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (559 reviews)
"A nice safe and quiet place to stay. Park right in front of your door. My dog loved the large grass area. The room was large and the beds very comfortable. The heat was on when we arrived which was great . It was cold and snowy that day. I loved having the self check-in and check out. We plan on going back the next time we are in the area. "
United States
SUSAN
The price is Rp1.906.630
Rp2.129.706 total
includes taxes & fees
18 May - 19 May
The Little Lion

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (177 reviews)
"Great staff. "
United States
wesley
The price is Rp2.698.748
Rp3.103.560 total
includes taxes & fees
12 May - 13 May
Blackberry River Inn

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,004 reviews)
"Great location "
United States
Edith
The price is Rp2.018.050
Rp2.254.162 total
includes taxes & fees
25 May - 26 May
Quality Inn Lee - Lenox South

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (92 reviews)
"Room was clean, bed was comfortable, pool was nice, breakfast and coffee were good!"
United States
Haley
The price is Rp2.051.076
Rp2.291.121 total
includes taxes & fees
17 May - 18 May
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
9.8 out of 10, Exceptional, (6 reviews)
"The new owners have done a great job. The place is immaculate, the room was very comfortable and well appointed, the common areas charming. Highly recommended."
United States
Robert
The price is Rp3.288.937
Rp3.673.903 total
includes taxes & fees
18 May - 19 May
The Berkshire Mountain Inn

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
"enjoy your vacation"
United States
lev
The price is Rp2.620.858
Rp3.015.323 total
includes taxes & fees
12 May - 13 May
The Cornell Inn, Lenox & The Berkshires

The Whitlock

The Whitlock
2.0 star property
Lenox
8.6 out of 10, Excellent, (295 reviews)
"Lovely historical hotel within walking distance to many great shops and restaurants. Staff members maintained good communication and were very helpful throughout our stay. Rooms were clean, quiet, and comfortable. Would definitely stay there again."
United States
Elaine
The price is Rp1.995.454
Rp2.228.922 total
includes taxes & fees
11 May - 12 May
The Whitlock
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Stay near popular Sheffield attractions

Learn more about Sheffield

Tucked in the Berkshires, this charming town offers scenic hikes at Bartholomew's Cobble and local art at the Sheffield Historical Society. Catch live performances at the Berkshire Theatre Festival in nearby Stockbridge or sample farm-fresh produce at the weekend farmers' market on the town green.

FTYTP1 The Upper Sheffield Covered Bridge, Sheffield, Massachusetts, USA

Top Sheffield Hotel Reviews

More cheap stays in Sheffield

Find out more about Sheffield

Top reasons to visit Sheffield

  • Outdoor Adventures: Sheffield is a haven for outdoor enthusiasts, offering skiing, hiking, and exploring picturesque lakes and nature reserves.
  • Family-Friendly Activities: Enjoy apple picking and exciting rides, making it ideal for memorable family outings.
  • Art and Culture: Discover a variety of art galleries that showcase local talent and creativity.
  • Charming Atmosphere: Experience the warmth of friendly locals and a welcoming community in the beautiful Berkshires.
  • Diverse Accommodation: From agritourism to cosy bed and breakfasts, Sheffield has unique stays catering to every traveller.

Find great hotels near Sheffield

Experience the charm of Sheffield, Massachusetts, with a variety of accommodation options that cater to every traveller's needs. From delightful agritourism properties to inviting bed and breakfasts, Sheffield offers pet-friendly and family-oriented stays perfect for your adventure. Explore nearby attractions while enjoying a comfortable retreat in this picturesque town, with additional options available in Great Barrington for an unforgettable holiday experience.

  • Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: This charming 3.5-star resort offers a delightful blend of leisure and adventure, making it an ideal choice for families and business travellers alike. Nestled 19.3km from Sheffield, the resort features a variety of amenities, including an onsite mini-golf course, an arcade game room, and a playground to keep children entertained. The proximity to ski shuttles and lifts ensures that winter sports enthusiasts can easily access the slopes. With spacious accommodations and family-friendly services, this resort is perfect for a memorable vacation in the Berkshires.
  • Quality Inn: Located 9.7km from Sheffield, Quality Inn is the perfect base for adventure seekers and business travellers. Guests can enjoy a range of outdoor activities, from downhill skiing to hiking and biking, all available in the surrounding areas. The hotel’s focus on adventure sports makes it an exciting option for those looking to explore the natural beauty of the region. With comfortable lodging and easy access to recreational facilities, Quality Inn caters to those with an adventurous spirit while providing essential amenities for a productive stay.
  • Holiday Inn Express Hotel & Suites Great Barrington by IHG: Situated 11.3km from Sheffield, this hotel welcomes travellers with its inclusive atmosphere and modern comforts. Known for being LGBTQIA-friendly, it provides a warm environment for all guests. The property is well-equipped for business travel, featuring meeting spaces and complimentary Wi-Fi. Guests appreciate the contemporary design and convenient location, which offers easy access to local attractions. With attentive service and a focus on providing a comfortable experience, this hotel is an excellent choice for both leisure and business stays.

Where to stay near Sheffield

Sheffield, Massachusetts, offers an enchanting blend of adventure and history, perfect for an outdoor getaway. Nestled in the beautiful Berkshires, visitors can revel in stunning scenery, charming evenings, and a family-friendly atmosphere. Nearby attractions provide a romantic vibe, with friendly locals enhancing the experience. Whether you seek thrilling activities or a relaxing retreat, Sheffield and its surroundings promise a memorable stay, complemented by some of the best hotels in the region.

  • The Berkshires: Nestled 17.7km from Sheffield, The Berkshires is a stunning region renowned for its breathtaking outdoor experiences, making it a perfect destination for adventure seekers. With a blend of scenic mountains and serene lakes, this area is ideal for skiing in the winter and hiking in the summer. The Berkshires is not only about natural beauty—it's also home to various cultural events and venues, including conferences and festivals, which attract visitors year-round, particularly in the warmer months from June to August.
  • Great Barrington: Located 9.7km from Sheffield, Great Barrington is a vibrant city that draws visitors with its dynamic outdoor lifestyle and sporting opportunities. Known for its excellent skiing facilities, this area is a favourite among winter sports enthusiasts. During your visit, explore the local parks and lakes that offer tranquil spots for relaxation and picnicking. Great Barrington sees a peak in visitors from June to August, making it an exciting summer destination that balances adventure with community events.
  • South Egremont: Just 8.0km from Sheffield, South Egremont is a charming city that invites adventure lovers to experience its ski resorts and recreational activities. This area, like its neighbours, boasts stunning landscapes featuring mountains and lakes, perfect for both winter sports and summer excursions. South Egremont attracts a steady stream of visitors throughout the year, with a notable influx during the summer months. The nearby national state park offers additional opportunities for exploration and immersion in nature.

Things to do near Sheffield

Sheffield, Massachusetts, offers a delightful mix of outdoor adventures and family-friendly activities. Visitors can enjoy skiing at local resorts, partake in apple picking, and explore various art galleries. The area is perfect for day trips and exciting rides, making it an ideal destination for memorable family outings amidst the beautiful New England scenery.

Shopping

In Sheffield, you can enjoy shopping at local gems like Hoffman's Pottery for unique items. If you're up for a drive, Lee Premium Outlets, located 22.5km away, offers a variety of brand-name stores, while the Berkshire Mountain Country Store, 24.1km away, features charming local goods.

Recreation

Lake Mansfield Park, a tranquil retreat 11.3km from Sheffield, offers serene walking trails and picturesque views, perfect for relaxation. Music Mountain, located 20.9km away, hosts vibrant concerts, while Undermountain Golf Course, 14.5km from town, provides an invigorating outdoor experience for golf enthusiasts.

Adventure

At Ski Butternut, 8.0km from Sheffield, experience exhilarating skiing amidst a vibrant sports atmosphere. The Housatonic River Walk, located 9.7km away, offers breathtaking scenery for hikers seeking outdoor adventure. For thrill-seekers, Catamount Aerial Adventure Park, 12.9km from Sheffield, features an exciting zipline and ropes course.

Nightlife

In Sheffield, the Mahaiwe Performing Arts Center offers a charming atmosphere with captivating performances just 9.7km away. Infinity Music Hall and Bistro, located 17.7km away, blends exquisite dining with live entertainment. For a rich cultural experience, the Berkshire Theatre Festival is only 19.3km from Sheffield.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Sheffield

To save money on your trip to Sheffield, consider visiting during the off-peak months of January and March to April, when accommodation prices are lower. Booking your stay for a Tuesday can also help you find cheaper rates, while Saturdays tend to be the most expensive. Use Expedia’s search tool to filter by budget, location, and hotel type, including eco-certified options. You can further save by bundling your hotel, flights, and activities into a package deal, ensuring you get the best value for your stay.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Sheffield are January and March to April, where the prices are slightly lower. This is in comparison to July to August and October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Sheffield is Tuesday. The most expensive day to stay in Sheffield is Saturday.
  • Find cheap hotels on Expedia: Expedia’s search tool enables you to set your budget, choose your ideal location, and much more. You can arrange your search results to display prices from lowest to highest, allowing you to find the most affordable hotels first. Additionally, you can refine your choices by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels available for booking.
  • Consider bundling your trip: You can save money by combining your hotel reservation in Sheffield with your flights and activities through an Expedia package.

Find the best attractions near Sheffield

Sheffield, Massachusetts, is an excellent destination for adventure seekers and outdoor enthusiasts, offering a variety of activities such as skiing and exploring nature. Visitors can enjoy nearby national parks, nature reserves, and picturesque lakes, making it ideal for eco-friendly experiences. Whether you’re hiking, skiing, or simply soaking in the natural beauty, Sheffield promises an unforgettable outdoor vacation.

  • Bash Bish Falls State Park: Located 11.3km away from Sheffield, this stunning park features breathtaking waterfalls surrounded by lush greenery. It offers a perfect blend of adventure and tranquillity, with hiking trails that lead you through picturesque landscapes.
  • Housatonic River: Just 9.7km from Sheffield, the Housatonic River is a serene spot ideal for picnicking and scenic walks. Its beautiful banks provide a peaceful atmosphere where you can enjoy the natural beauty and perhaps spot some local wildlife.
  • Three Mile Pond Wildlife Management Area: Only 3.2km from Sheffield, this nature reserve is an eco-friendly haven. It's perfect for outdoor enthusiasts seeking adventure, with opportunities for birdwatching and exploring diverse habitats.

Best time to go to Sheffield

The best time to visit Sheffield is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January23.2°F (-4.9°C)Light RainMostly CloudyAverageSlightly Low
February24.8°F (-4.0°C)Light RainMostly CloudySlightly LowAverage
March32.5°F (0.3°C)Light RainMostly CloudyAverageSlightly Low
April44.2°F (6.8°C)Light RainMostly CloudyAverageSlightly Low
May55.9°F (13.3°C)Light RainMostly SunnyAverageAverage
June63.7°F (17.6°C)Light RainMostly SunnySlightly HighAverage
July69.8°F (21.0°C)Light RainMostly SunnySlightly HighSlightly High
August67.8°F (19.9°C)Light RainMostly SunnyAverageSlightly High
September60.8°F (16.0°C)Light RainMostly SunnySlightly HighAverage
October49.8°F (9.9°C)Light RainMostly SunnyAverageSlightly High
November37.8°F (3.2°C)Light RainMostly SunnySlightly LowAverage
December29.7°F (-1.3°C)Light RainMostly CloudySlightly LowAverage

The nearest major airports for your trip to Sheffield

To visit Sheffield, Massachusetts, you can fly into several major airports. Hartford, CT (BDL-Bradley Intl.) is 59.5km away, with nearby hotels such as the Sheraton Hartford Hotel at Bradley Airport and The Capitol Hotel, both offering convenient access via airport shuttles. Albany, NY (ALB-Albany Intl.) is 80.5km distant, featuring hotels like Oakcliff Bed and Breakfast and Four Points by Sheraton Albany, easily reachable from the airport. Finally, Newburgh, NY (SWF-Stewart Intl.) is 91.7km away, with options like The Crossroads Hotel and Comfort Suites Fishkill, both accessible via local transportation services. Each airport provides a variety of accommodation choices to enhance your stay.

Frequently asked questions

Where is the best place to stay in Sheffield?
Wilder House Berkshires is one of the top choices for your stay based on our traveller data. This B&B offers free breakfast and free parking. Two other options for your trip to the area are Berkshire Mountain Lodge and Berkshires Untold. See all available top hotels, or vacation rentals in Sheffield.
If I need to cancel my hotel reservation in Sheffield, will I receive a refund?
Yes, the majority of hotel reservations are fully refundable provided that you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If your reservation is non-refundable, it may still be possible to cancel it and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Sheffield.
What are some accommodation options with pools in Sheffield?
Berkshire Mountain Lodge: Offers free self parking, an indoor pool and complimentary wireless Internet access. The Red Lion Inn and Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG are a couple of other choices that feature an on-site pool. View all hotels with pools in Sheffield.
What's it like staying in Sheffield?
Visitors can enjoy all that Sheffield has to offer, including the casinos and local tours. In Sheffield, there are 33 hotels and other accommodation options to choose from. Find out more about Sheffield.
What are the top places to visit in Sheffield?
Favourite places to visit include Housatonic River, Magnolia Bluffs Casino and Mount Everett State Reservation. A couple of additional sights to add to your itinerary are Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife Sanctuary. Take a look at what more there is to see and do in Expedia's Sheffield guide.
What's the seasonal weather like in Sheffield?
The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Sheffield are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

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